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Light emitting material, delayed fluorescent emitter, organic light emitting device, and compound

a light emitting device and fluorescent technology, applied in the direction of organic chemistry, thiazine dyes, acridine dyes, etc., to achieve excellent light emission characteristics

Active Publication Date: 2017-06-20
KYULUX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The xanthone derivative provides a high light emission efficiency and can be used as a delayed fluorescent material, significantly improving the performance of organic light emitting devices by emitting delayed fluorescent light with a high quantum efficiency.

Problems solved by technology

However, Non-patent Document 1 does not describe the light emission characteristics of the compounds that have an analogous skeleton other than fluorenone.

Method used

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  • Light emitting material, delayed fluorescent emitter, organic light emitting device, and compound
  • Light emitting material, delayed fluorescent emitter, organic light emitting device, and compound
  • Light emitting material, delayed fluorescent emitter, organic light emitting device, and compound

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of Compound 1

[0173]The compound 1 was synthesized according to the following procedures.

[0174]

[0175]In a three-neck flask equipped with a Dean-Stark trap, phenol (12.35 g, 131.25 mmol), K2CO3 (34.55 g, 250 mmol), N,N-dimethylformamide (125 mL) and toluene (125 mL) were charged, and refluxed in a nitrogen atmosphere for 4 hours to perform dehydration until no further water was formed from the reaction system. Thereafter, 100 mL of toluene was removed with the Dean-Stark trap.

[0176]After returning to room temperature, 4-bromo-2-fluorobenzonitrile (25.0 g, 125 mmol) was added thereto, and the mixture was refluxed in a nitrogen atmosphere for 4 hours. After completing the reaction, the solution was diluted by adding toluene (200 mL) thereto, and then filtered with Celite. The solution was rinsed twice with water with a separating funnel, dried over anhydrous magnesium sulfate, and filtered. The product was purified by silica gel chromatography (mobile phase: toluene / ethyl acet...

synthesis example 2

Synthesis of Compound 4

[0187]The compound 4 was synthesized according to the following procedures.

[0188]

[0189]In a three-neck flask equipped with a Dean-Stark trap, 3-bromophenol (22.72 g, 131.3 mmol), K2CO3 (34.55 g, 250 mmol), N,N-dimethylformamide (130 mL) and toluene (130 mL) were charged, and refluxed in a nitrogen atmosphere for 4 hours to perform dehydration until no further water was formed from the reaction system. Thereafter, 100 mL of toluene was removed with the Dean-Stark trap.

[0190]After returning to room temperature, 4-bromo-2-fluorobenzonitrile (25.0 g, 125 mmol) was added thereto, and the mixture was refluxed in a nitrogen atmosphere for 4 hours. After completing the reaction, the solution was diluted by adding toluene (200 mL) thereto, and then filtered with Celite. The solution was rinsed twice with water with a separating funnel, dried over anhydrous magnesium sulfate, and filtered. The product was purified by silica gel chromatography (mobile phase: toluene / ethy...

synthesis example 3

Synthesis of Compound 2

[0204]The synthesis was performed according to the following reaction scheme in the same manner as is the compound 1 in Example 1 (yield: 97%).

[0205]

[0206]In a two-neck flask, the compound 1b (0.83 g, 3 mmol), 9,9-dimethyl-10-(4-(4,4,5,5-tetramethyl-, 3,2-dioxaborolan-2-yl)phenyl)-9.10-dihydroacridine (1.36 g, 3.3 mmol), 3 mL of a 2M aqueous solution of potassium carbonate, 6 mL of 1,2-dimethoxyethane, 6 mL of toluene, and tetrakis(triphenylphosphine) palladium (104 mg, 0.09 mmol) were charged, and refluxed in a nitrogen atmosphere for 48 hours.

[0207]After completing the reaction, the reaction solution was extracted with dichloromethane with a separating funnel, dried over anhydrous magnesium sulfate, then filtered, and concentrated. The product was purified by silica gel chromatography (mobile phase: dichloromethane). The product was further rinsed with 30 mL of an ethyl acetate / n-hexane mixed solvent (1 / 1) under application of ultrasonic wave for 5 minutes, ...

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Abstract

A compound represented by the following general formula is useful as a light emitting material. X represents an oxygen atom or a sulfur atom. R1 to R8 represent a hydrogen atom or a substituent, provided that at least one of R1 to R8 is a carbazolyl group, etc.

Description

TECHNICAL FIELD[0001]The present invention relates to a compound that is useful as a light emitting material, and an organic light emitting device using the same.BACKGROUND ART[0002]An organic light emitting device, such as an organic electroluminescent device (organic EL device), has been actively studied for enhancing the light emission efficiency thereof. In particular, various studies for enhancing the light emitting efficiency have been made by newly developing and combining an electron transporting material, a hole transporting material, a light emitting material and the like constituting an organic electroluminescent device. There are studies relating to an organic electroluminescent device utilizing a fluorenone derivative.[0003]Non-patent Document 1 describes the results of the studies on the solution light emission characteristics of the compound having a diarylamino group introduced to at least one of the 2- and 7-positions of fluorenone. According thereto, there is descr...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07D405/04C07D413/14C09B57/00C09B21/00C09B19/00C09B17/02C07D405/14C07D405/10H01L51/00C09K11/06C07D409/04C07D409/10C07D491/107C07D495/10C07D519/00C09B11/28C09B15/00H01L51/50H10K99/00
CPCH01L51/0072C07D405/04C07D405/10C07D405/14C07D409/04C07D409/10C07D413/14C07D491/107C07D495/10C07D519/00C09B11/28C09B15/00C09B17/02C09B19/00C09B21/00C09B57/00C09K11/06H01L51/005H01L51/0071H01L51/0073C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1088C09K2211/145H01L51/5012H10K85/60H10K85/6574H10K85/6572H10K85/657H10K50/11
Inventor NUMATA, MASAKIYASUDA, TAKUMALEE, JIYOUNGYOSHIZAKI, ASUKAADACHI, CHIHAYA
Owner KYULUX INC
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